Furano pyrimidines as novel potent and selective anti-VZV agents

McGuigan, Christopher ORCID: https://orcid.org/0000-0001-8409-710X, Brancale, Andrea ORCID: https://orcid.org/0000-0002-9728-3419, Barucki, H., Srinivasan, S, Jones, G., Pathirana, Ranjith N., Carangio, A., Blewett, S., Luoni, G., Bidet, O., Jukes, A., Jarvis, C., Andrei, G., Snoeck, R., De Clercq, E. and Balzarini, J. 2001. Furano pyrimidines as novel potent and selective anti-VZV agents. Antiviral chemistry & chemotherapy 12 (2) , pp. 77-89.

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Abstract

Bicyclic furano pyrimidine nucleosides have been found to be highly potent and selective inhibitors of varicella zoster virus (VZV). They are inactive against herpes simplex virus and have been known for several decades as (unwanted) synthetic by-products in the Pd-catalysed coupling of acetylenes to 5-iodo nucleosides. These fluorescent bicyclic nucleosides are now established as a new family of potent antivirals. They are unusual in that they exhibit complete specificity for VZV and require an alkyl (or alkylaryl) side-chain for biological activity. The latter requirement confers extremely high lipophilicities on these compounds, unknown amongst chemotherapeutic nucleosides, which may be of considerable importance in formulation, dosing and tissue distribution. The most potent compounds reported are p-alkylaryl compounds, with EC50 values below 1 nM versus VZV and selectivity index values of around 1,000,000. Here, we review the discovery, synthesis, characterization, antiviral profile, SAR, mechanism of action and development prospects for this new family of antivirals.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Pharmacy Systems Immunity Research Institute (SIURI)
Subjects:	R Medicine > RS Pharmacy and materia medica
Uncontrolled Keywords:	VZV ; furanopyrimidines ; shingles ; chickenpox
ISSN:	0956-3202
Last Modified:	05 Jan 2024 05:59
URI:	https://orca.cardiff.ac.uk/id/eprint/7487

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